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pubmed-article:19123794pubmed:abstractTextA nontraditional approach to the enantiocontrolled construction of quaternary center-bearing heteroatom-bridged bicyclo[3.3.1]nonanes (homotropanes) is reported that is based on organometallic enantiomeric scaffolding. This strategy takes advantage of the unique reactivity profiles of TpMo(CO)(2)(5-oxo-eta(3)-pyranyl) and TpMo(CO)(2)(5-oxo-eta(3)-pyridinyl) scaffolds, and features a molybdenum-mediated semipinacol/1,5-"Michael-like" reaction sequence to establish the quaternary center and synthesize the bridged bicyclic structure. An asymmetric total synthesis of (-)-adaline highlights this methodology.lld:pubmed
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pubmed-article:19123794pubmed:articleTitleOrganometallic enantiomeric scaffolding. Sequential semipinacol/1,5-"Michael-like" reactions as a strategic approach to bridgehead-quaternary center aza[3.3.1]bicyclics: application to the total synthesis of (-)-adaline.lld:pubmed
pubmed-article:19123794pubmed:affiliationSanford S. Atwood Chemistry Center, Emory University, 1515 Dickey Drive, Atlanta, Georgia 30322, USA.lld:pubmed
pubmed-article:19123794pubmed:publicationTypeJournal Articlelld:pubmed
pubmed-article:19123794pubmed:publicationTypeResearch Support, N.I.H., Extramurallld:pubmed
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